5 questions to ask before making a career change

We make choices regularly. Some are easy while others require a longer time for decisions.


What happens then if you are stuck with uncertainty?

There isn’t any clarity in your career pathway.


You have only heard a story that is superbly inspiring like this young Singapore lady who manages to find her career footing in Guatemala.


Should you switch your job to seize better future opportunities?


Evaluating the advantages and disadvantages is part of analyzing your career pivoting choices. To know what this means, we need to first acknowledge the meaning of career change:


a change to a different type of job from the one you have been doing

(Source: Cambridge dictionary)


Making a career change at 30 years old can be different if one has a change of career at 40 years old.


Here is an example:


30 years old camp


Objective: Career progression

Question: Which career suits me?

Plan: Find a job that offers me opportunities to scale up


40 years old camp


Objective: A meaningful purpose in my career

Question: What should I do to make a smooth transition?

Plan: Identify occupations that fit right into my “purpose” and “career”


Common self-assessment:


(a) Should I change industries?

(b) What’s my career pivot strategy that leads me to a high chance of success?

(c) Do I have the capabilities to perform in my new role?

(d) What if the choice is wrong? I have my commitments


I know of a mid-career lady who is 43 years old and is a mother of two kids. She is the Marketing Manager of a consumer goods firm for the last 9 years. She is keen to look for a flexible role that offers her the opportunity to work from home, as well as manage the demands from her work.


Secondly, she wants a new challenge. She is wondering whether a change to a Digital Marketer will fit her well. However, she did not possess any deep knowledge yet.


It’s easy to point her to a direction of skill upgrading immediately. However, we have not assessed her inner motivation, except for the drivers to make a pivoting decision.


For instance, what type of “demands” is she referring to?


What does career mean to her right now?


Granted that Covid-19 forces us the way we work now, there may be more than what she thinks, apart from staggering work hours. Therefore, a 1:1 consultation is important to flesh out her deeper thoughts, to steer her towards an actionable plan that makes the transition smooth. In the end, she chooses not to change after discussing it with me.


Instead, she aims to speak to 5 contacts in the digital marketing field, gather the insights, and go to an online crash course to understand how the dynamics of digital marketing is done first. It’s about research and interpretation.


It also dawns upon her that this is just a little interest but not to a full-blown career passion yet. As for her job scope, she turns to her boss to request for a set of “no-pay leave” days per month. The green light is given since she has performed well during her tenure in the company. What these examples highlight is that there can be several moving parts.


How then will you be able to develop some quick answers?

Consider these 5 questions first:


1) How comfortable are you with the new position?


By that, I mean the tasks that you need to do. It’s not as simple as looking up in Google, watch a YouTube video, or go to Udemy to take an online course. You need to be accustomed to a brand new industry language, terms used, and the materials are given.


That’s why the RIASEC test by Dr. John Holland is a great way to uncover your interest level.


If you are Singaporean or PR, you can get the test for free in your Skill Future portal. Use your SingPass to login. There are also other complimentary RIASEC assessments placed on the internet. But one needs to decipher the depth and quality before jumping on it.


Someone good at fixing things may not be at ease dealing with abstract data analysis such as A.I. and robotics.


Another way is to get your friends to vouch for you. They should have an idea of what you like to do and enjoy doing.


Ask 5 of your great buddies who know you for years.


2) What is the key driver that pushes you to change?


Many may respond to “money”.


Yeah, many prefer a high growth career prospect such as a Data Scientist remuneration package.


Problem is, you don’t get your hands on it daily. Drag your feet daily to complete the work tasks? Think about it.


To find out the underlying “push” factor is to travel back in time. Look back at your entire corporate experiences. Name 3 dislikes that you have personal control on but just didn’t work out for you.


Bad bosses, toxic work culture not valid here since it’s not possible to anticipate such changes.


From the 3, name your biggest unhappiness that keeps you up at night. Then, write a short statement to explain your rationale.


If this is hard to imagine, get an experienced Career Coach like myself to help you.


For me, I deal with cases on this frequently. From a mid-level Manager who finds that 75% of her time is spent on administrative responsibilities (which are repetitive chores to her) to Senior Managers who find that bugging people is not his cup of tea.


What I do best is to turn things around by developing a framework that guides my clients towards maximum clarity. Then, implement the process by taking small action steps to minimize the dislikes. Spot job specifications that lean towards the “likes”.


We can’t of course avoid specific tasks if it’s within your occupation but this shouldn’t be more than a huge % of your work.


Some may prefer 85% likes, 15% dislikes.


In short, your key driver has to be strong and sustainable to make the ultimate switch.


Banging on a techie trend that isn’t the right fit will mean your career satisfaction level decreases.


3) How long do you think you can breathe in this position?


Will you get jaded from the demands and expectations of the new role?


Talk to people in the same trade to find out more.


We have Zoom now, that’s convenient to invite your contact for a 30 minutes conference call. People do like to share their stories in confidence.


Another great way is to ascertain your adaptability to anything new.


For example, you will like to pick up a new cooking recipe (e.g. Mexican dishes), something interesting assuming your culinary skills are almost zero. Your objective is to complete the dish within 45 minutes.


Congratulations if you make it!


If not, perhaps you may find it challenging during the process. Which part of it is the obstacle?


The concept is similar to work.


Would you have the luxury of time?


Some may be overwhelmed by software navigation but this is one of the key criteria in the new job. The changing demand for a role adds pressure. Your boss just adds to the fuel by chasing you down. To prevent this, find out how quickly you can react to specific things, people or data – just like the cooking illustration above.


Do a trial if it’s possible.


Some new IT software has 7 days free. At least you can practice hands-on to check whether new features are something that relates to you easily in a specific time frame.


4) Which are the top 3 skills that I can bring over to this new position?


Having interpersonal abilities, communication techniques are needed in most jobs but it may be too generic.


It’s just doesn’t bring out clear visibility – who doesn’t possess the knowledge to talk to people? But communicating with C-suite and getting intellectual responses back? That’s a new level. It’s the specific skill point and the competency matrix that is important.


Think about your unique skills that distinguish you from the rest. Then, scan the potential job opportunities through LinkedIn. Identify the keywords from the requirements that other positions will not have. Revert to your skill profile. Is there a match?

You can also use the free resource through My Skills Framework.


Understand the type of skill level needed in each designated role. Cross-compare with your top 3 to assess further.


I did a one-to-one skill assessment for a Logistics Manager in the past. He is an operational guy. One of his core abilities flagged out is the knowledge in workflow management.


Hence, he uses these words “workflow management” to search on LinkedIn. He manages to find a suitable fit from a list.


Usually, the fit doesn’t have to be 100% but most of it should align. Send me an email if you think I can help you and I’ll certainly respond to you very soon.


5) What’s the level of expectation in this role?


If you are one who finds it hard to perform in a fast-moving environment, you will not be pivoting to a consumer goods industry.


The expectation has to be understood in the beginning. It’s about the job and yourself.


Talk to people with experiences in the sector. Gather a brief list of short questions. Google is your best friend too. There are forums such as Quora to check out.

After gathering the information, one has to do a self-check-in accepting a possible change in the following:


(a) Remuneration

(b) Gaps in your new role as compared to your previous job

(c) Your ability to perform within a specific period


The objective is to come to terms with the shifts. That can be done by writing down the 3 core motivators (read: drivers) that leads you to assume the new role.


Career pivoting in the 30s to 40s have different diverse needs. Answering the 5 questions will begin the journey of awareness. Gradually, you should see answers popping up. A holistic career conversation helps to facilitate the process.


Just make sure your career change decision has undergone rounds of analysis and not just an over-the-top consideration.

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